Electrophilic Halogen Reagents-mediated Halogenation: Synthesis of Halogenated Dihydro-1,3-oxazine Derivatives DOI

Liang Qi,

Yuji Qin,

Xueqing Wang

et al.

Chemical Research in Chinese Universities, Journal Year: 2022, Volume and Issue: 39(6), P. 933 - 947

Published: Nov. 21, 2022

Language: Английский

Electrochemical oxidative radical cascade reactions for the synthesis of difluoromethylated benzoxazines DOI

Xiang Chen,

Jun Jiang, Xiaojun Huang

et al.

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 10(15), P. 3898 - 3902

Published: Jan. 1, 2023

An efficient electrochemical synthesis of fluoroethylated benzoxazines via oxyfluoromethylation was developed. The broad applicability and general utility were tested highlighted by the substrate scope late-stage synthesis.

Language: Английский

Citations

25
Radical-mediated alkoxypolyhaloalkylation of styrenes with polyhaloalkanes and alcohols via C(sp3)–H bond cleavage DOI

Yunyan Liang,

Jing Huang, Xuan‐Hui Ouyang

et al.

Chemical Communications, Journal Year: 2021, Volume and Issue: 57(30), P. 3684 - 3687

Published: Jan. 1, 2021

A radical-mediated alkoxypolyhaloalkylation of styrenes with polychloroalkanes and alcohols for the facile synthesis complex polyhaloalkanes excellent functional-group compatibility a broad substrate scope.

Language: Английский

Citations

44
Metal-Catalyst-Free Radical Cyclization of 1,6-Enynes for the Selective and Switchable Synthesis of Lactams in Water DOI

Xuan-Chi Yu,

Yan‐Nan Zheng,

Jun-Hao Zhang

et al.

ACS Sustainable Chemistry & Engineering, Journal Year: 2022, Volume and Issue: 10(18), P. 6057 - 6062

Published: April 27, 2022

Three types of novel radical cyclization 1,6-enynes with sulfonyl hydrazides have been presented, which provided convenient synthetic approaches for accessing five-membered cyclic lactams, lactams containing C–I bond, and six-membered lactams. Notably, these transformations are implemented in metal-catalyst-free systems, three classes important lactam derivatives were synthesized selectivity controllability from the same substrate using water as green solvent.

Language: Английский

Citations

35
Visible-Light Induced Organophotocatalysis for the Synthesis of Difluoroethylated Benzoxazines DOI Open Access
Xiang Chen, Wen‐Tao Ouyang, Xiao Li

et al.

Chinese Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 43(12), P. 4213 - 4213

Published: Jan. 1, 2023

Benzoxazines are important motif in pharmaceuticals and functional molecules.A visible-light induced photocatalytic strategy for the synthesis of difluoroethyl benzoxazines with organo-photocatalyst was developed.In present protocol, a series olefinic amides can be transferred to difluoroethylated via oxydifluoromethylation CF2HSO2Na as difluoromethylating reagent, which is easily operated good group tolerant.

Language: Английский

Citations

20
Iron-Mediated Bromocyclization of Olefinic Amides for the Synthesis of Bromobenzoxazines DOI

Tong‐Tong Zhao,

Qiang Bian, Da‐Zhen Xu

et al.

Synthesis, Journal Year: 2024, Volume and Issue: 56(19), P. 2993 - 3000

Published: June 5, 2024

Abstract An iron-mediated bromination/cyclization for the synthesis of bromobenzoxazines from olefinic amides has been successfully developed. In this protocol, simple iron salt FeBr3 was employed as a bromination reagent, giving bromobenzoxazine products in moderate to excellent yields. This methodology features good functional group tolerance, gram-scale synthesis, and green reaction conditions by use air terminal oxidant. Preliminary mechanistic studies suggest that free radical pathway is involved.

Language: Английский

Citations

3
Highly efficient and fast synthesis of di-iodinated succinimide derivatives from 1,6-enyne and I2 under air at room temperature DOI

Yuling Lu,

Chunmei Chen, Hucheng Zhu

et al.

Green Chemistry, Journal Year: 2022, Volume and Issue: 24(20), P. 8021 - 8028

Published: Jan. 1, 2022

A metal-free, additive-free, and practical method for the synthesis of diiodinated succinimide derivatives has been achieved under mild conditions.

Language: Английский

Citations

15
Green Tandem [5C + 1C] Cycloaromatization of α-Alkenoyl Ketene Dithioacetals and Nitroethane in Water: Eco-Friendly Synthesis of Ortho-Acylphenols DOI
Haifeng Yu, Zheyu Zhang, Xue Zhang

et al.

The Journal of Organic Chemistry, Journal Year: 2022, Volume and Issue: 87(5), P. 2985 - 2996

Published: Feb. 8, 2022

For the first time, an eco-friendly and sustainable tandem [5C + 1C] cycloaromatization of α-alkenoyl ketene dithioacetals nitroethane in water for efficient synthesis ortho-acylphenols was reported. In refluxing water, a range smoothly underwent Michael addition/cyclization/aromatization reactions presence 2.0 equivalents DBU to provide various excellent yields. The green approach not only avoided use harmful organic solvents, which could result serious environmental safety issues, but also exhibited fascinating features such as good substrate scope, yields, simple purification desired products, ease scale-up, reusable aqueous medium.

Language: Английский

Citations

10
Synthesis of Polycyclic Quinazolinones through C(sp3)−H Functionalization of Inert Alkanes or Visible‐Light‐Promoted Oxidation Decarboxylation of N‐Hydroxyphthalimide Esters DOI
Weikang Zhang,

Jiao‐Zhe Li,

Cancan Zhang

et al.

European Journal of Organic Chemistry, Journal Year: 2022, Volume and Issue: 2022(35)

Published: May 20, 2022

Abstract Two novel C(sp 3 )−H functionalization of inert alkanes and visible‐light promoted oxidation decarboxylation N ‐hydroxyphthalimide (NHP) esters to access polycyclic quinazolinones have been described. These methods do not involve metal catalysts are carried out in water or water/DMSO media. The wide substrate scope, even including the seven‐membered ring under mild reaction conditions, demonstrate practicability these strategies.

Language: Английский

Citations

10
Uncatalyzed diastereoselective synthesis of alkyliminofurochromone-derived benzylmalononitriles via a three-component cascade reaction: competition between Diels–Alder cycloaddition and Michael addition DOI
Mohammad Bagher Teimouri,

Zahra Mokhtare,

Hamid Reza Khavasi

et al.

Organic & Biomolecular Chemistry, Journal Year: 2021, Volume and Issue: 19(11), P. 2517 - 2525

Published: Jan. 1, 2021

Three new chemical bonds and three stereogenic centres one heterocyclic ring were assembled stereoselectively in a convenient high atom-economy one-pot operation.

Language: Английский

Citations

10
Synthesis of 2,4-Dicyanoalkylated Benzoxazines through the Radical-Mediated Cascade Cyclization of Isocyanides with AIBN under Metal- and Additive-Free Conditions DOI

Mengjia Ni,

Shuanggen Gui,

Yang Fu

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(6), P. 3970 - 3976

Published: Feb. 29, 2024

A general and novel method for the radical cascade cyclization of aryl isocyanides with AIBN has been described. This strategy provides straightforward access to various 2,4-dicyanoalkylated benzoxazines in moderate good yields under metal- additive-free conditions. The reaction can apply a gram scale tolerate diverse functional groups. 2,4-Dicyanoalkylated benzoxazine derivatives feature large Stokes shift intramolecular charge transfer properties.

Language: Английский

Citations

1